(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Base Information

Chemical Name:(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide
CAS No.:862888-57-1
Molecular Formula:C₄₅H₅₈N₂O₈Si
Molecular Weight:783.05
Hs Code.:

Synonyms:(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

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Technology Process of (Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

There total 4 articles about (Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.1%

: 862888-52-6
(Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoic acid

: 78-96-6,1674-56-2
3-amino-2-propanol

: 862888-57-1
(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 23.5h;
DOI:10.1248/cpb.53.529

Reference yield:

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 862888-57-1
(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: Multi-step reaction with 3 steps

1: 67.3 percent / DBU / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / aq. NaOH / dioxane / 19.5 h / 20 °C

3: 85.1 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; 1-hydroxybenzotriazole; N-ethyldiisopropylamine / CH₂Cl₂ / 23.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; 1: Horner-Emmons reaction;
DOI:10.1248/cpb.53.529

Reference yield:

: 78009-77-5
2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose

: 862888-57-1
(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: Multi-step reaction with 3 steps

1: 67.3 percent / DBU / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / aq. NaOH / dioxane / 19.5 h / 20 °C

3: 85.1 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; 1-hydroxybenzotriazole; N-ethyldiisopropylamine / CH₂Cl₂ / 23.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; 1: Horner-Emmons reaction;
DOI:10.1248/cpb.53.529